Structure and spectroscopic properties of the dimeric copper(I) N-heterocyclic carbene complex [Cu₂(CNC_t-Bu)₂](PF₆)₂

In recent years, the use of copper N-heterocyclic carbene (NHC) complexes has expanded to fields besides catalysis, namely medicinal chemistry and lumin­escence applications. In the latter case, multinuclear copper NHC compounds have attracted inter­est, however, the number of these complexes in the literature is still quite limited. Bis­[μ-1,3-bis­(3-tert-butyl­imidazolin-2-yliden-1-yl)pyri­dine]-1κ⁴C²,N:N,C^2′;2κ⁴C²,N:N,C^2′-dicopper(I) bis­(hexa­fluorido­phos­phate), [Cu₂(C₁₉H₂₅N₅)₂](PF₆)₂, is a dimeric copper(I) complex bridged by two CNC, i.e. bis­(N-heterocyclic carbene)pyridine, ligands. Each Cu^I atom is almost linearly coordinated by two NHC ligands and inter­actions are observed between the pyridine N atoms and the metal centres, while no cuprophilic inter­actions were observed. Very strong absorption bands are evident in the UV–Vis spectrum at 236 and 274 nm, and an emission band is observed at 450 nm. The reported complex is a new example of a multinuclear copper NHC complex and a member of a compound class which has only rarely been reported.

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

Bis[µ-1,3-bis(3-tert-butylimidazolin-2-yliden-1-yl)pyridine]-1κ⁴C²,N:N,C^2';2κ⁴C²,N:N,C^2'-dicopper(I) bis(hexafluoridophosphate)

Crystal data

[Cu2(C19H25N5)2](PF6)2	F(000) = 1088
Mr = 1063.92	Dx = 1.554 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9245 reflections
a = 8.9698 (4) Å	θ = 2.3–25.4°
b = 12.4288 (5) Å	µ = 1.10 mm^−1
c = 20.3978 (8) Å	T = 123 K
β = 90.7276 (17)°	Fragment, yellow
V = 2273.84 (16) Å^3	0.20 × 0.20 × 0.18 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	7815 independent reflections
Radiation source: rotating anode FR591	7559 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16 pixels mm^-1	θmax = 25.4°, θmin = 1.9°
phi– and ω–rotation scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2008b)	k = −13→14
Tmin = 0.639, Tmax = 0.745	l = −24→24
32544 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.023P)^2 + 0.3225P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.049	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.35 e Å^−3
7815 reflections	Δρmin = −0.25 e Å^−3
589 parameters	Absolute structure: Flack x determined using 3250 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.025 (3)

Special details

Experimental. Diffractometer operator A. Poethig scanspeed 10 s per frame dx 50 2461 frames measured in 7 data sets phi-scan with delta_phi = 0.5 omega-scans with delta_omega = 0.5

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3672 (3)	0.3828 (2)	0.30873 (12)	0.0194 (5)
C2	0.2877 (3)	0.5528 (2)	0.32639 (15)	0.0269 (6)
H2	0.2719	0.6195	0.3480	0.032*
C3	0.2381 (3)	0.5266 (2)	0.26661 (14)	0.0267 (6)
H3	0.1810	0.5703	0.2374	0.032*
C4	0.2550 (3)	0.3570 (2)	0.20029 (12)	0.0203 (5)
C5	0.1398 (3)	0.3816 (2)	0.15684 (13)	0.0265 (6)
H5	0.0792	0.4434	0.1629	0.032*
C6	0.1164 (3)	0.3131 (3)	0.10447 (13)	0.0317 (7)
H6	0.0397	0.3283	0.0733	0.038*
C7	0.2039 (3)	0.2227 (2)	0.09721 (12)	0.0261 (6)
H7	0.1888	0.1744	0.0616	0.031*
C8	0.3145 (3)	0.2052 (2)	0.14374 (11)	0.0200 (5)
C9	0.5637 (3)	0.1213 (2)	0.14770 (11)	0.0187 (5)
C10	0.3672 (3)	0.0129 (2)	0.11941 (12)	0.0253 (6)
H10	0.2684	−0.0104	0.1100	0.030*
C11	0.4919 (3)	−0.0461 (2)	0.11727 (13)	0.0261 (6)
H11	0.4980	−0.1203	0.1064	0.031*
C12	0.4377 (3)	0.4605 (2)	0.41941 (12)	0.0253 (6)
C13	0.4297 (4)	0.5710 (3)	0.45178 (17)	0.0481 (9)
H13A	0.4739	0.5672	0.4959	0.072*
H13B	0.3252	0.5935	0.4547	0.072*
H13C	0.4848	0.6233	0.4255	0.072*
C14	0.3509 (5)	0.3790 (3)	0.45883 (14)	0.0537 (11)
H14A	0.3510	0.3096	0.4360	0.081*
H14B	0.2480	0.4039	0.4637	0.081*
H14C	0.3976	0.3707	0.5022	0.081*
C15	0.5989 (3)	0.4284 (3)	0.41247 (14)	0.0366 (7)
H15A	0.6044	0.3550	0.3952	0.055*
H15B	0.6488	0.4314	0.4554	0.055*
H15C	0.6482	0.4779	0.3823	0.055*
C16	0.7691 (3)	−0.0191 (2)	0.13313 (14)	0.0269 (6)
C17	0.7981 (4)	−0.0632 (3)	0.06404 (14)	0.0390 (8)
H17A	0.7316	−0.1242	0.0553	0.059*
H17B	0.9020	−0.0870	0.0612	0.059*
H17C	0.7793	−0.0066	0.0316	0.059*
C18	0.7840 (4)	−0.1078 (2)	0.18460 (14)	0.0372 (8)
H18A	0.7646	−0.0778	0.2281	0.056*
H18B	0.8851	−0.1375	0.1838	0.056*
H18C	0.7117	−0.1649	0.1750	0.056*
C19	0.8768 (4)	0.0722 (3)	0.1483 (2)	0.0459 (9)
H19A	0.8658	0.1284	0.1149	0.069*
H19B	0.9793	0.0447	0.1482	0.069*
H19C	0.8549	0.1022	0.1915	0.069*
C20	0.5192 (3)	0.0976 (2)	0.32398 (12)	0.0198 (5)
C21	0.5703 (3)	−0.0747 (2)	0.35270 (13)	0.0276 (6)
H21	0.5558	−0.1489	0.3616	0.033*
C22	0.6989 (3)	−0.0218 (2)	0.35766 (13)	0.0272 (6)
H22	0.7928	−0.0503	0.3710	0.033*
C23	0.7714 (3)	0.1702 (2)	0.34059 (12)	0.0203 (5)
C24	0.8847 (3)	0.1735 (2)	0.38714 (12)	0.0264 (6)
H24	0.8983	0.1169	0.4179	0.032*
C25	0.9777 (3)	0.2624 (2)	0.38711 (12)	0.0274 (6)
H25	1.0570	0.2675	0.4183	0.033*
C26	0.9554 (3)	0.3440 (2)	0.34184 (12)	0.0239 (6)
H26	1.0185	0.4054	0.3409	0.029*
C27	0.8373 (3)	0.3323 (2)	0.29803 (11)	0.0186 (5)
C28	0.7295 (3)	0.39332 (19)	0.19321 (11)	0.0169 (5)
C29	0.8421 (3)	0.5217 (2)	0.25701 (12)	0.0226 (6)
H29	0.8936	0.5549	0.2926	0.027*
C30	0.7922 (3)	0.5693 (2)	0.20220 (13)	0.0234 (6)
H30	0.8020	0.6433	0.1914	0.028*
C31	0.2999 (3)	−0.0338 (2)	0.32793 (13)	0.0274 (6)
C32	0.2463 (4)	−0.0552 (3)	0.39761 (14)	0.0409 (8)
H32A	0.3052	−0.1135	0.4172	0.061*
H32B	0.1409	−0.0758	0.3962	0.061*
H32C	0.2584	0.0102	0.4240	0.061*
C33	0.2887 (4)	−0.1354 (2)	0.28524 (15)	0.0396 (8)
H33A	0.3282	−0.1201	0.2416	0.059*
H33B	0.1840	−0.1573	0.2811	0.059*
H33C	0.3466	−0.1935	0.3057	0.059*
C34	0.2078 (3)	0.0544 (2)	0.29586 (15)	0.0344 (7)
H34A	0.2112	0.1190	0.3233	0.052*
H34B	0.1043	0.0302	0.2909	0.052*
H34C	0.2484	0.0709	0.2526	0.052*
C35	0.6671 (3)	0.5086 (2)	0.09468 (12)	0.0222 (6)
C36	0.6473 (3)	0.6290 (2)	0.08285 (14)	0.0300 (6)
H36A	0.5811	0.6590	0.1161	0.045*
H36B	0.6035	0.6407	0.0392	0.045*
H36C	0.7446	0.6648	0.0857	0.045*
C37	0.5178 (4)	0.4520 (3)	0.08520 (15)	0.0385 (8)
H37A	0.5304	0.3747	0.0929	0.058*
H37B	0.4811	0.4639	0.0403	0.058*
H37C	0.4458	0.4810	0.1163	0.058*
C38	0.7851 (4)	0.4638 (3)	0.04866 (13)	0.0322 (7)
H38A	0.8805	0.4999	0.0572	0.048*
H38B	0.7539	0.4763	0.0031	0.048*
H38C	0.7964	0.3863	0.0562	0.048*
Cu1	0.65265 (3)	0.25288 (2)	0.17613 (2)	0.02084 (8)
Cu2	0.44658 (3)	0.23909 (2)	0.30313 (2)	0.02059 (8)
N1	0.8035 (2)	0.41376 (16)	0.25137 (9)	0.0176 (4)
N2	0.7230 (2)	0.49038 (16)	0.16371 (10)	0.0179 (4)
N3	0.7459 (2)	0.24704 (18)	0.29607 (8)	0.0179 (4)
N4	0.6675 (2)	0.08422 (16)	0.33919 (10)	0.0209 (5)
N5	0.3666 (2)	0.46555 (17)	0.35174 (10)	0.0216 (5)
N6	0.2877 (2)	0.42173 (16)	0.25583 (10)	0.0201 (5)
N7	0.3414 (2)	0.26938 (16)	0.19476 (9)	0.0176 (4)
N8	0.4123 (2)	0.11531 (16)	0.13831 (9)	0.0188 (4)
N9	0.6110 (3)	0.02060 (16)	0.13376 (10)	0.0220 (5)
N10	0.4606 (3)	−0.00234 (16)	0.33216 (10)	0.0217 (5)
F1	0.7040 (2)	0.20907 (18)	0.85814 (10)	0.0581 (6)
F2	0.8564 (2)	0.33528 (15)	0.90314 (13)	0.0625 (6)
F3	0.9528 (3)	0.21121 (17)	0.97045 (10)	0.0636 (6)
F4	0.8035 (3)	0.08549 (15)	0.92442 (12)	0.0677 (7)
F5	0.9513 (2)	0.18348 (19)	0.86187 (11)	0.0645 (6)
F6	0.7053 (3)	0.2355 (3)	0.96609 (11)	0.0838 (8)
P1	0.82903 (8)	0.20983 (5)	0.91432 (3)	0.02482 (16)
F7	0.0895 (2)	0.32186 (13)	0.56208 (8)	0.0356 (4)
F8	0.23879 (19)	0.19908 (16)	0.61254 (8)	0.0442 (5)
F9	0.0039 (2)	0.22401 (15)	0.64763 (7)	0.0412 (4)
F10	0.0635 (2)	0.07107 (13)	0.59484 (8)	0.0411 (4)
F11	0.1505 (2)	0.16775 (13)	0.50990 (7)	0.0370 (4)
F12	−0.08418 (19)	0.19439 (14)	0.54515 (8)	0.0400 (4)
P2	0.07736 (8)	0.19649 (5)	0.57857 (3)	0.02208 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0192 (14)	0.0178 (13)	0.0214 (12)	0.0002 (10)	0.0022 (10)	0.0007 (10)
C2	0.0267 (16)	0.0156 (13)	0.0384 (16)	0.0017 (11)	0.0057 (13)	−0.0034 (11)
C3	0.0256 (16)	0.0156 (13)	0.0389 (16)	0.0053 (11)	0.0045 (12)	0.0036 (11)
C4	0.0206 (14)	0.0207 (13)	0.0195 (12)	−0.0010 (10)	0.0028 (10)	0.0020 (10)
C5	0.0196 (15)	0.0317 (15)	0.0281 (14)	0.0075 (11)	0.0002 (11)	0.0057 (12)
C6	0.0220 (16)	0.0489 (19)	0.0241 (14)	0.0061 (13)	−0.0054 (12)	0.0041 (12)
C7	0.0214 (14)	0.0362 (17)	0.0207 (12)	−0.0010 (11)	−0.0048 (10)	−0.0039 (11)
C8	0.0172 (13)	0.0213 (13)	0.0216 (12)	−0.0013 (10)	0.0021 (10)	0.0029 (10)
C9	0.0210 (14)	0.0173 (12)	0.0177 (11)	−0.0004 (10)	−0.0019 (10)	0.0013 (10)
C10	0.0308 (16)	0.0227 (14)	0.0223 (13)	−0.0109 (11)	−0.0016 (11)	−0.0048 (11)
C11	0.0384 (18)	0.0143 (13)	0.0257 (13)	−0.0074 (11)	−0.0002 (12)	−0.0041 (11)
C12	0.0262 (15)	0.0293 (15)	0.0204 (13)	−0.0045 (11)	0.0031 (11)	−0.0085 (11)
C13	0.044 (2)	0.049 (2)	0.051 (2)	0.0060 (16)	−0.0068 (16)	−0.0295 (17)
C14	0.064 (3)	0.077 (3)	0.0200 (15)	−0.037 (2)	0.0026 (15)	0.0000 (16)
C15	0.0372 (18)	0.0449 (18)	0.0274 (15)	0.0067 (14)	−0.0061 (13)	−0.0102 (13)
C16	0.0299 (17)	0.0175 (13)	0.0334 (15)	0.0086 (11)	0.0000 (12)	−0.0012 (11)
C17	0.044 (2)	0.0453 (19)	0.0281 (15)	0.0174 (15)	0.0019 (14)	0.0018 (14)
C18	0.049 (2)	0.0326 (17)	0.0302 (15)	0.0131 (14)	−0.0056 (14)	0.0036 (13)
C19	0.0233 (17)	0.0319 (17)	0.082 (3)	0.0070 (13)	−0.0023 (16)	−0.0063 (17)
C20	0.0242 (15)	0.0176 (13)	0.0176 (12)	−0.0023 (10)	−0.0001 (10)	0.0023 (10)
C21	0.0412 (18)	0.0141 (13)	0.0274 (14)	0.0046 (12)	0.0023 (12)	0.0070 (11)
C22	0.0357 (17)	0.0196 (14)	0.0261 (13)	0.0073 (12)	−0.0003 (12)	0.0079 (11)
C23	0.0233 (14)	0.0186 (13)	0.0189 (12)	0.0025 (10)	−0.0005 (10)	0.0017 (10)
C24	0.0275 (15)	0.0307 (15)	0.0210 (13)	0.0033 (12)	−0.0048 (11)	0.0077 (11)
C25	0.0255 (14)	0.0351 (16)	0.0215 (12)	−0.0012 (12)	−0.0072 (10)	−0.0001 (12)
C26	0.0218 (15)	0.0297 (15)	0.0202 (12)	−0.0048 (11)	−0.0013 (11)	−0.0019 (11)
C27	0.0199 (14)	0.0197 (13)	0.0161 (11)	0.0011 (10)	0.0019 (10)	−0.0012 (10)
C28	0.0164 (13)	0.0165 (12)	0.0178 (11)	−0.0007 (10)	−0.0006 (10)	−0.0002 (10)
C29	0.0281 (15)	0.0165 (13)	0.0232 (13)	−0.0054 (11)	−0.0005 (11)	−0.0053 (10)
C30	0.0273 (16)	0.0128 (12)	0.0303 (14)	−0.0038 (10)	0.0010 (12)	−0.0015 (11)
C31	0.0334 (18)	0.0225 (14)	0.0263 (14)	−0.0104 (12)	0.0018 (12)	0.0008 (11)
C32	0.040 (2)	0.052 (2)	0.0312 (16)	−0.0179 (15)	0.0073 (14)	0.0027 (15)
C33	0.052 (2)	0.0274 (16)	0.0396 (17)	−0.0120 (14)	−0.0015 (15)	−0.0026 (13)
C34	0.0259 (16)	0.0322 (17)	0.0448 (17)	−0.0069 (13)	−0.0055 (13)	0.0032 (13)
C35	0.0245 (15)	0.0210 (13)	0.0209 (13)	0.0000 (11)	−0.0043 (11)	0.0042 (10)
C36	0.0357 (17)	0.0223 (14)	0.0321 (15)	0.0048 (12)	−0.0007 (12)	0.0109 (12)
C37	0.0320 (18)	0.0433 (19)	0.0398 (17)	−0.0152 (14)	−0.0163 (14)	0.0206 (15)
C38	0.0383 (18)	0.0380 (17)	0.0204 (13)	0.0127 (13)	−0.0029 (12)	0.0006 (12)
Cu1	0.02063 (16)	0.01273 (15)	0.02898 (15)	−0.00104 (12)	−0.00649 (11)	−0.00168 (13)
Cu2	0.02219 (16)	0.01424 (15)	0.02524 (15)	0.00120 (12)	−0.00417 (11)	0.00081 (13)
N1	0.0202 (12)	0.0164 (10)	0.0163 (10)	−0.0025 (8)	−0.0016 (8)	0.0000 (8)
N2	0.0198 (12)	0.0143 (11)	0.0195 (10)	−0.0014 (8)	−0.0014 (9)	0.0012 (8)
N3	0.0206 (10)	0.0170 (10)	0.0162 (9)	0.0004 (9)	−0.0010 (7)	0.0000 (9)
N4	0.0257 (13)	0.0171 (11)	0.0198 (10)	0.0026 (9)	−0.0011 (9)	0.0052 (8)
N5	0.0212 (12)	0.0193 (11)	0.0244 (11)	−0.0008 (9)	0.0030 (9)	−0.0056 (9)
N6	0.0216 (12)	0.0153 (11)	0.0235 (11)	0.0024 (9)	0.0013 (9)	0.0014 (9)
N7	0.0173 (11)	0.0177 (11)	0.0177 (9)	−0.0007 (8)	−0.0009 (8)	0.0012 (8)
N8	0.0207 (12)	0.0172 (10)	0.0184 (10)	−0.0024 (9)	−0.0016 (8)	−0.0020 (8)
N9	0.0274 (13)	0.0139 (10)	0.0248 (11)	0.0003 (9)	−0.0001 (9)	−0.0021 (9)
N10	0.0279 (13)	0.0161 (11)	0.0211 (11)	−0.0033 (9)	0.0009 (9)	0.0025 (9)
F1	0.0433 (12)	0.0755 (15)	0.0551 (11)	−0.0055 (10)	−0.0184 (9)	0.0054 (11)
F2	0.0468 (13)	0.0201 (9)	0.1203 (19)	0.0017 (8)	−0.0104 (12)	0.0091 (11)
F3	0.0701 (15)	0.0579 (14)	0.0617 (12)	−0.0132 (11)	−0.0398 (11)	0.0022 (10)
F4	0.0974 (19)	0.0271 (11)	0.0780 (15)	−0.0217 (11)	−0.0219 (14)	0.0088 (10)
F5	0.0419 (13)	0.0831 (17)	0.0692 (14)	0.0032 (11)	0.0247 (10)	−0.0210 (12)
F6	0.0620 (14)	0.119 (2)	0.0715 (14)	−0.0342 (15)	0.0372 (11)	−0.0552 (15)
P1	0.0264 (4)	0.0196 (3)	0.0285 (3)	−0.0007 (3)	0.0002 (3)	−0.0032 (3)
F7	0.0391 (11)	0.0230 (9)	0.0448 (10)	−0.0023 (7)	0.0031 (8)	0.0018 (7)
F8	0.0300 (10)	0.0578 (12)	0.0445 (10)	0.0044 (8)	−0.0132 (8)	−0.0039 (9)
F9	0.0496 (11)	0.0472 (11)	0.0271 (8)	0.0063 (9)	0.0088 (7)	−0.0006 (8)
F10	0.0642 (13)	0.0254 (9)	0.0335 (9)	−0.0014 (8)	−0.0025 (8)	0.0091 (7)
F11	0.0542 (12)	0.0337 (9)	0.0233 (8)	0.0093 (8)	0.0078 (7)	0.0025 (7)
F12	0.0292 (10)	0.0457 (11)	0.0448 (10)	−0.0062 (8)	−0.0129 (8)	0.0074 (8)
P2	0.0249 (4)	0.0216 (3)	0.0197 (3)	−0.0001 (3)	−0.0014 (3)	0.0020 (3)

Geometric parameters (Å, º)

C1—N5	1.352 (3)	C23—N3	1.335 (3)
C1—N6	1.374 (3)	C23—C24	1.383 (4)
C1—Cu2	1.927 (3)	C23—N4	1.418 (3)
C2—C3	1.333 (4)	C24—C25	1.385 (4)
C2—N5	1.391 (4)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.384 (4)
C3—N6	1.396 (3)	C25—H25	0.9500
C3—H3	0.9500	C26—C27	1.385 (4)
C4—N7	1.342 (3)	C26—H26	0.9500
C4—C5	1.387 (4)	C27—N3	1.340 (3)
C4—N6	1.417 (3)	C27—N1	1.420 (3)
C5—C6	1.380 (4)	C28—N2	1.349 (3)
C5—H5	0.9500	C28—N1	1.376 (3)
C6—C7	1.380 (4)	C28—Cu1	1.907 (2)
C6—H6	0.9500	C29—C30	1.337 (4)
C7—C8	1.381 (3)	C29—N1	1.390 (3)
C7—H7	0.9500	C29—H29	0.9500
C8—N7	1.331 (3)	C30—N2	1.397 (3)
C8—N8	1.426 (3)	C30—H30	0.9500
C9—N9	1.353 (3)	C31—N10	1.495 (4)
C9—N8	1.370 (3)	C31—C34	1.516 (4)
C9—Cu1	1.907 (2)	C31—C32	1.529 (4)
C10—C11	1.339 (4)	C31—C33	1.536 (4)
C10—N8	1.389 (3)	C32—H32A	0.9800
C10—H10	0.9500	C32—H32B	0.9800
C11—N9	1.390 (3)	C32—H32C	0.9800
C11—H11	0.9500	C33—H33A	0.9800
C12—C15	1.508 (4)	C33—H33B	0.9800
C12—N5	1.515 (3)	C33—H33C	0.9800
C12—C14	1.515 (4)	C34—H34A	0.9800
C12—C13	1.526 (4)	C34—H34B	0.9800
C13—H13A	0.9800	C34—H34C	0.9800
C13—H13B	0.9800	C35—N2	1.506 (3)
C13—H13C	0.9800	C35—C37	1.523 (4)
C14—H14A	0.9800	C35—C36	1.526 (4)
C14—H14B	0.9800	C35—C38	1.529 (4)
C14—H14C	0.9800	C36—H36A	0.9800
C15—H15A	0.9800	C36—H36B	0.9800
C15—H15B	0.9800	C36—H36C	0.9800
C15—H15C	0.9800	C37—H37A	0.9800
C16—N9	1.502 (4)	C37—H37B	0.9800
C16—C19	1.520 (4)	C37—H37C	0.9800
C16—C18	1.527 (4)	C38—H38A	0.9800
C16—C17	1.537 (4)	C38—H38B	0.9800
C17—H17A	0.9800	C38—H38C	0.9800
C17—H17B	0.9800	Cu1—N7	2.8298 (18)
C17—H17C	0.9800	Cu2—N7	2.4220 (18)
C18—H18A	0.9800	Cu1—N3	2.5765 (17)
C18—H18B	0.9800	Cu2—N3	2.6923 (18)
C18—H18C	0.9800	F1—P1	1.5929 (19)
C19—H19A	0.9800	F2—P1	1.595 (2)
C19—H19B	0.9800	F3—P1	1.5849 (19)
C19—H19C	0.9800	F4—P1	1.5761 (19)
C20—N10	1.361 (3)	F5—P1	1.576 (2)
C20—N4	1.372 (3)	F6—P1	1.574 (2)
C20—Cu2	1.921 (2)	F7—P2	1.5981 (17)
C21—C22	1.330 (4)	F8—P2	1.5975 (18)
C21—N10	1.394 (4)	F9—P2	1.5997 (16)
C21—H21	0.9500	F10—P2	1.5989 (17)
C22—N4	1.399 (3)	F11—P2	1.5950 (16)
C22—H22	0.9500	F12—P2	1.5937 (17)
N5—C1—Cu2	138.46 (19)	C26—C27—N1	120.8 (2)
N6—C1—Cu2	117.93 (17)	N2—C28—N1	103.7 (2)
N9—C9—Cu1	136.6 (2)	C30—C29—N1	106.1 (2)
N8—C9—Cu1	119.92 (18)	C30—C29—H29	127.0
N10—C20—Cu2	137.1 (2)	N1—C29—H29	127.0
N4—C20—Cu2	119.11 (18)	C29—C30—N2	107.5 (2)
N2—C28—Cu1	136.33 (18)	C29—C30—H30	126.2
N1—C28—Cu1	119.73 (17)	N2—C30—H30	126.2
C9—Cu1—C28	171.67 (10)	N10—C31—C34	110.8 (2)
C20—Cu2—C1	163.74 (10)	N10—C31—C32	107.8 (2)
C20—Cu2—N7	118.13 (9)	C34—C31—C32	110.5 (3)
C1—Cu2—N7	76.70 (9)	N10—C31—C33	107.7 (2)
C8—N7—Cu2	133.26 (16)	C34—C31—C33	108.6 (2)
C4—N7—Cu2	105.55 (14)	C32—C31—C33	111.4 (2)
N5—C1—N6	103.6 (2)	C31—C32—H32A	109.5
C3—C2—N5	108.2 (2)	C31—C32—H32B	109.5
C3—C2—H2	125.9	H32A—C32—H32B	109.5
N5—C2—H2	125.9	C31—C32—H32C	109.5
C2—C3—N6	105.6 (2)	H32A—C32—H32C	109.5
C2—C3—H3	127.2	H32B—C32—H32C	109.5
N6—C3—H3	127.2	C31—C33—H33A	109.5
N7—C4—C5	123.5 (2)	C31—C33—H33B	109.5
N7—C4—N6	114.4 (2)	H33A—C33—H33B	109.5
C5—C4—N6	122.1 (2)	C31—C33—H33C	109.5
C6—C5—C4	117.6 (2)	H33A—C33—H33C	109.5
C6—C5—H5	121.2	H33B—C33—H33C	109.5
C4—C5—H5	121.2	C31—C34—H34A	109.5
C5—C6—C7	120.3 (2)	C31—C34—H34B	109.5
C5—C6—H6	119.9	H34A—C34—H34B	109.5
C7—C6—H6	119.9	C31—C34—H34C	109.5
C6—C7—C8	117.3 (2)	H34A—C34—H34C	109.5
C6—C7—H7	121.3	H34B—C34—H34C	109.5
C8—C7—H7	121.3	N2—C35—C37	109.3 (2)
N7—C8—C7	124.4 (2)	N2—C35—C36	109.4 (2)
N7—C8—N8	115.1 (2)	C37—C35—C36	109.4 (2)
C7—C8—N8	120.5 (2)	N2—C35—C38	107.1 (2)
N9—C9—N8	103.5 (2)	C37—C35—C38	111.6 (2)
C11—C10—N8	105.7 (2)	C36—C35—C38	109.9 (2)
C11—C10—H10	127.1	C35—C36—H36A	109.5
N8—C10—H10	127.1	C35—C36—H36B	109.5
C10—C11—N9	107.7 (2)	H36A—C36—H36B	109.5
C10—C11—H11	126.1	C35—C36—H36C	109.5
N9—C11—H11	126.1	H36A—C36—H36C	109.5
C15—C12—N5	108.6 (2)	H36B—C36—H36C	109.5
C15—C12—C14	111.8 (3)	C35—C37—H37A	109.5
N5—C12—C14	107.3 (2)	C35—C37—H37B	109.5
C15—C12—C13	109.2 (3)	H37A—C37—H37B	109.5
N5—C12—C13	109.6 (2)	C35—C37—H37C	109.5
C14—C12—C13	110.2 (3)	H37A—C37—H37C	109.5
C12—C13—H13A	109.5	H37B—C37—H37C	109.5
C12—C13—H13B	109.5	C35—C38—H38A	109.5
H13A—C13—H13B	109.5	C35—C38—H38B	109.5
C12—C13—H13C	109.5	H38A—C38—H38B	109.5
H13A—C13—H13C	109.5	C35—C38—H38C	109.5
H13B—C13—H13C	109.5	H38A—C38—H38C	109.5
C12—C14—H14A	109.5	H38B—C38—H38C	109.5
C12—C14—H14B	109.5	C28—N1—C29	111.5 (2)
H14A—C14—H14B	109.5	C28—N1—C27	122.9 (2)
C12—C14—H14C	109.5	C29—N1—C27	125.6 (2)
H14A—C14—H14C	109.5	C28—N2—C30	111.2 (2)
H14B—C14—H14C	109.5	C28—N2—C35	124.3 (2)
C12—C15—H15A	109.5	C30—N2—C35	124.0 (2)
C12—C15—H15B	109.5	C23—N3—C27	116.5 (2)
H15A—C15—H15B	109.5	C20—N4—C22	111.5 (2)
C12—C15—H15C	109.5	C20—N4—C23	123.2 (2)
H15A—C15—H15C	109.5	C22—N4—C23	125.1 (2)
H15B—C15—H15C	109.5	C1—N5—C2	111.0 (2)
N9—C16—C19	110.6 (2)	C1—N5—C12	123.7 (2)
N9—C16—C18	107.8 (2)	C2—N5—C12	125.3 (2)
C19—C16—C18	110.4 (3)	C1—N6—C3	111.6 (2)
N9—C16—C17	107.2 (2)	C1—N6—C4	121.9 (2)
C19—C16—C17	109.8 (3)	C3—N6—C4	126.4 (2)
C18—C16—C17	111.0 (2)	C8—N7—C4	116.9 (2)
C16—C17—H17A	109.5	C9—N8—C10	111.9 (2)
C16—C17—H17B	109.5	C9—N8—C8	123.8 (2)
H17A—C17—H17B	109.5	C10—N8—C8	124.2 (2)
C16—C17—H17C	109.5	C9—N9—C11	111.1 (2)
H17A—C17—H17C	109.5	C9—N9—C16	127.2 (2)
H17B—C17—H17C	109.5	C11—N9—C16	121.6 (2)
C16—C18—H18A	109.5	C20—N10—C21	110.7 (2)
C16—C18—H18B	109.5	C20—N10—C31	127.3 (2)
H18A—C18—H18B	109.5	C21—N10—C31	121.7 (2)
C16—C18—H18C	109.5	F6—P1—F5	179.23 (13)
H18A—C18—H18C	109.5	F6—P1—F4	90.35 (16)
H18B—C18—H18C	109.5	F5—P1—F4	89.33 (14)
C16—C19—H19A	109.5	F6—P1—F3	90.38 (14)
C16—C19—H19B	109.5	F5—P1—F3	90.32 (13)
H19A—C19—H19B	109.5	F4—P1—F3	91.02 (12)
C16—C19—H19C	109.5	F6—P1—F1	89.31 (13)
H19A—C19—H19C	109.5	F5—P1—F1	89.99 (12)
H19B—C19—H19C	109.5	F4—P1—F1	89.21 (12)
N10—C20—N4	103.7 (2)	F3—P1—F1	179.62 (14)
C22—C21—N10	108.3 (2)	F6—P1—F2	90.51 (15)
C22—C21—H21	125.9	F5—P1—F2	89.80 (13)
N10—C21—H21	125.9	F4—P1—F2	179.12 (15)
C21—C22—N4	105.8 (2)	F3—P1—F2	89.14 (12)
C21—C22—H22	127.1	F1—P1—F2	90.63 (12)
N4—C22—H22	127.1	F12—P2—F11	90.15 (10)
N3—C23—C24	124.3 (2)	F12—P2—F8	179.57 (12)
N3—C23—N4	114.7 (2)	F11—P2—F8	90.26 (10)
C24—C23—N4	120.9 (2)	F12—P2—F7	89.42 (10)
C23—C24—C25	117.4 (2)	F11—P2—F7	90.20 (10)
C23—C24—H24	121.3	F8—P2—F7	90.45 (10)
C25—C24—H24	121.3	F12—P2—F10	90.01 (10)
C26—C25—C24	120.2 (2)	F11—P2—F10	89.88 (9)
C26—C25—H25	119.9	F8—P2—F10	90.12 (10)
C24—C25—H25	119.9	F7—P2—F10	179.42 (12)
C25—C26—C27	117.1 (2)	F12—P2—F9	89.87 (10)
C25—C26—H26	121.4	F11—P2—F9	179.41 (10)
C27—C26—H26	121.4	F8—P2—F9	89.72 (10)
N3—C27—C26	124.4 (2)	F7—P2—F9	90.39 (10)
N3—C27—N1	114.7 (2)	F10—P2—F9	89.52 (10)